WO2002068539A1 - Phthalimidyl azo dyes, process for the preparation thereof and the use thereof - Google Patents

Phthalimidyl azo dyes, process for the preparation thereof and the use thereof Download PDF

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Publication number
WO2002068539A1
WO2002068539A1 PCT/EP2002/000904 EP0200904W WO02068539A1 WO 2002068539 A1 WO2002068539 A1 WO 2002068539A1 EP 0200904 W EP0200904 W EP 0200904W WO 02068539 A1 WO02068539 A1 WO 02068539A1
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WO
WIPO (PCT)
Prior art keywords
formula
dye
dyes
synthetic
materials
Prior art date
Application number
PCT/EP2002/000904
Other languages
English (en)
French (fr)
Inventor
Antoine Clément
Jean-Claude Wilhelm
Alfons Arquint
Urs Lauk
Original Assignee
Ciba Specialty Chemicals Holding Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Specialty Chemicals Holding Inc. filed Critical Ciba Specialty Chemicals Holding Inc.
Priority to KR1020037010374A priority Critical patent/KR100840884B1/ko
Priority to US10/467,263 priority patent/US7087731B2/en
Priority to AT02719738T priority patent/ATE496973T1/de
Priority to JP2002568642A priority patent/JP4205951B2/ja
Priority to DE60239044T priority patent/DE60239044D1/de
Priority to EP02719738A priority patent/EP1358274B1/en
Priority to PL02362752A priority patent/PL362752A1/xx
Publication of WO2002068539A1 publication Critical patent/WO2002068539A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
    • C09B29/0033—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with one nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0805—Amino benzenes free of acid groups
    • C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
    • C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
    • C09B43/42—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms by substituting radicals containing hetero atoms for —CN radicals

Definitions

  • the present invention relates to disperse dyes having an N-butyl-phthalimide-diazo component and an aniline coupling component, to processes for the preparation of such dyes and to the use thereof in dyeing or printing semi-synthetic and especially synthetic hydrophobic fibre materials, especially textile materials.
  • Disperse azo dyes having an N-alkyl-phthalimide-diazo component and an aniline coupling component have been known for a long time and are used in dyeing hydrophobic fibre materials. It has, however, been found that the dyeings or prints obtained using the currently known dyes do not in all cases satisfy today's requirements, especially in respect of fastness to washing and fastness to perspiration. There is therefore a need for new dyes that especially have good washing fastness properties.
  • the present invention accordingly relates to disperse dyes that yield dyeings having a high degree of fastness to washing and to perspiration and that, in addition, have good build-up characteristics both in the exhaust and thermosol processes and in textile printing.
  • the dyes are also suitable for discharge printing.
  • the dyes according to the invention correspond to formula
  • R t is hydrogen, methyl or -NHCO-CrC 4 alkyl
  • R 2 is d-C 4 alkyl, it being possible for the alkyl chain, from C 2 upwards, optionally to be interrupted by an oxygen atom, and R 3 has, independently of R 2 , any of the meanings of R 2 .
  • Ri is preferably -NHCO-C C 4 alkyl.
  • C C Alkyl in the radical -NHCO-C C alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, especially methyl.
  • R 2 and R 3 as C C 4 alkyl are, each independently of the other, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl.
  • R 2 and R 3 preferably have the same meaning.
  • R 2 and R 3 are especially ethyl or the radical -CH 2 CH 2 -OCH 3 .
  • the present invention relates also to the process for the preparation of the dyes of formula (1) according to the invention.
  • the dyes are prepared, for example, by nitration of a phthalimide of formula in the acid range, as described, for example, on page 459 in Organic Synthesis, Collective Volume 2, (a Revised Edition of Annual Volumes X-XIX), J.Wiley & Sons, followed by alkylation of the resulting nitro compound, for example in accordance with a method described in Journal of Organic Chemistry 32 (1967) on page 1923, paragraph 3, and, for example after reductive treatment described on page 569 in Bull. Soc. Chim. de France 1957. conversion into an intermediate of formula
  • the intermediate of formula (51) is dihalogenated and is then, in an acid medium, diazotised and coupled to a compound of formula
  • R 1( R 2 and R 3 have the definitions and preferred meanings given above.
  • the halogen substituents are then replaced by cyano using similarly known methods.
  • the halogenation is carried out, for example, by reacting the compound of formula (51) first with sodium acetate in acetic acid and then with bromine in the same medium to form the corresponding dibromo compound.
  • the diazotisation of the compound of formula (51) is likewise carried out in a manner known perse, for example with sodium nitrite in an acidic, for example hydrochloric-acid-containing orsulfuric-acid-containing, aqueous medium.
  • the diazotisation may, however, also be carried out using other diazotisation agents, e.g. with nitrosylsulfuric acid.
  • an additional acid may be present in the reaction medium, e.g. phosphoric acid, sulfuric acid, acetic acid, propionic acid, hydrochloric acid or mixtures of such acids, e.g. mixtures of propionic acid and acetic acid.
  • the diazotisation is advantageously carried out at temperatures of from -10 to 30°C, for example from -10°C to room temperature.
  • the coupling of the diazotised compound of formula (51) to the coupling component of formula (52) is likewise effected in known manner, for example in an acidic, aqueous or aqueous-organic medium, advantageously at temperatures of from -10 to 30°C, especially below 10°C.
  • acids used are hydrochloric acid, acetic acid, propionic acid, sulfuric acid and phosphoric acid.
  • the reaction to form the final dyes is carried out by replacement of the two halogen atoms by cyano groups using methods known perse, for example using CuCN or mixtures of CuCN and an alkali metal cyanide in a solvent, for example dimethylformamide, dimethyl sulfoxide, dimethylacetamide, N-vinylpyrrolidone, sulfolane or pyridine.
  • a solvent for example dimethylformamide, dimethyl sulfoxide, dimethylacetamide, N-vinylpyrrolidone, sulfolane or pyridine.
  • the diazo components of formula (51) and the coupling components of formula (52) are known or can be prepared in a manner known perse.
  • the present invention relates also to dye mixtures comprising at least two structurally different azo dyes of formula (1).
  • the dye mixtures according to the invention comprising at least two structurally different azo dyes of formula (1) can be prepared, for example, by simply mixing the individual dyes, for example by mixing the dyes of formulae (2) and (3).
  • the amounts of the individual dyes in the dye mixtures according to the invention can vary within a wide range, for example from 95:5 to 5:95 parts by weight, especially from 70:30 to 30:70 parts by weight, more especially from 55:45 to 45:55 parts by weight of the individual dyes in a dye mixture comprising two azo dyes according to the invention.
  • Very special preference is given to dye mixtures comprising the dyes of formulae (2) and (3) in a ratio by weight of from 1.1 :0.9 to 0.9:1.1 , especially in a ratio by weight of 1:1.
  • the dyes and dye mixtures according to the invention may be used for dyeing or printing semi-synthetic and especially synthetic hydrophobic fibre materials, especially textile materials.
  • Textile materials composed of blend fabrics that comprise such semi-synthetic or synthetic hydrophobic fibre materials can also be dyed or printed using the dyes or dye mixtures according to the invention.
  • Semi-synthetic fibre materials that come into consideration are, especially, cellulose 2 1 / 2 - acetate and cellulose triacetate.
  • Synthetic hydrophobic fibre materials consist especially of linear, aromatic polyesters, for example those of terephthalic acid and glycols, especially ethylene glycol, or condensation products of terephthalic acid and 1 ,4-bis(hydroxymethyl)cyclohexane; of polycarbonates, e.g. those of ⁇ , ⁇ -dimethyl-4,4-dihydroxy-diphenylmethane and phosgene, and of fibres based on polyvinyl chloride and on polyamide.
  • polyester fibre materials are dyed in the exhaust process from an aqueous dispersion in the presence of customary anionic or non-ionic dispersants and, optionally, customary swelling agents (carriers) at temperatures of from 80 to 140°C.
  • Cellulose 2 1 / 2 -acetate is dyed preferably at from 65 to 85°C and cellulose triacetate at temperatures of from 65 to 115°C.
  • the dyes and dye mixtures according to the invention will not colour wool and cotton present at the same time in the dyebath or will colour such materials only slightly (very good reservation) so that they can also be used satisfactorily in the dyeing of polyester/wool and polyester/cellulosic fibre blend fabrics.
  • the dyes and dye mixtures according to the invention are suitable for dyeing in accordance with the thermosol process, in the exhaust process and for printing processes.
  • the said fibre materials can be in a variety of processing forms, e.g. in the form of fibres, yarns or nonwoven, woven or knitted fabrics.
  • the dye is ground so that its particle size is on average from 0.1 to 10 microns. Grinding can be carried out in the presence of dispersants. For example, the dried dye is ground together with a dispersant or kneaded into a paste form together with a dispersant and then dried in vacuo or by atomisation. After adding water, the resulting preparations can be used to prepare printing pastes and dyebaths.
  • the customary thickeners will be used, e.g. modified or unmodified natural products, for example alginates, British gum, gum arabic, crystal gum, locust bean flour, tragacanth, carboxymethyl cellulose, hydroxyethyl cellulose, starch or synthetic products, for example polyacrylamides, polyacrylic acid or copolymers thereof, or polyvinyl alcohols.
  • modified or unmodified natural products for example alginates, British gum, gum arabic, crystal gum, locust bean flour, tragacanth, carboxymethyl cellulose, hydroxyethyl cellulose, starch or synthetic products, for example polyacrylamides, polyacrylic acid or copolymers thereof, or polyvinyl alcohols.
  • the dyes and dye mixtures according to the invention impart to the said materials, especially to polyester materials, level colour shades having very good in-use fastness properties such as, especially, good fastness to light, fastness to heat setting, fastness to pleating, fastness to chlorine, and wet fastness, e.g. fastness to water, to perspiration and to washing; the finished dyeings are further characterised by very good fastness to rubbing. Special emphasis should be given to the good fastness properties of the dyeings obtained with respect to perspiration and, especially, to washing.
  • the dyes and dye mixtures according to the invention can also be used satisfactorily in producing mixed shades together with other dyes.
  • the dyes and dye mixtures according to the invention are also well suited to dyeing hydrophobic fibre materials from supercritical CO 2 .
  • the present invention relates to the above-mentioned use of the dyes and dye mixtures according to the invention as well as to a process for the dyeing or printing of semi-synthetic or synthetic hydrophobic fibre materials, especially textile materials, in which process a dye according to the invention is applied to the said materials or incorporated into them.
  • the said hydrophobic fibre materials are preferably textile polyester materials. Further substrates that can be treated by the process according to the invention and preferred process conditions can be found above in the more detailed description of the use of the dyes according to the invention.
  • the invention relates also to hydrophobic fibre materials, preferably polyester textile materials, dyed or printed by the said process.
  • the dyes according to the invention are, in addition, suitable for modern reproduction processes, e.g. thermotransfer printing.
  • the mixture is added dropwise, over the course of 10 minutes, to a mixture consisting of 6.30 g of glacial acetic acid, 0.58 g of 32 % hydrochloric acid, 11.00 g of ice-water and 5.00 g of a 31.1 % aqueous solution of the compound of formula at a temperature of 0-5°C and is stirred for 120 minutes. Then, over the course of
  • a 1 % dyeing (based on the dye and the substrate) is produced on woven polyester fabric by the high-temperature exhaust process at 130°C and is cleaned reductively.
  • the blue dyeing obtained in that manner has very good in-use fastness properties, especially excellent fastness to washing.
  • thermosol process 10 g/litre of dye, liquor pick-up 50 %, fixing temperature 210°C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Cephalosporin Compounds (AREA)
PCT/EP2002/000904 2001-02-07 2002-01-29 Phthalimidyl azo dyes, process for the preparation thereof and the use thereof WO2002068539A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
KR1020037010374A KR100840884B1 (ko) 2001-02-07 2002-01-29 프탈이미딜 아조 염료 및 이의 제조방법
US10/467,263 US7087731B2 (en) 2001-02-07 2002-01-29 Phthalimidyl azo dyes, process for the preparation thereof and the use thereof
AT02719738T ATE496973T1 (de) 2001-02-07 2002-01-29 Phthalimidyl-azofarbstoffe, verfahren zu deren herstellung und deren verwendung
JP2002568642A JP4205951B2 (ja) 2001-02-07 2002-01-29 フタルイミドイルアゾ染料、それらの製造方法およびそれらの使用
DE60239044T DE60239044D1 (de) 2001-02-07 2002-01-29 Phthalimidyl-azofarbstoffe, verfahren zu deren herstellung und deren verwendung
EP02719738A EP1358274B1 (en) 2001-02-07 2002-01-29 Phthalimidyl azo dyes, process for their preparation and the use thereof
PL02362752A PL362752A1 (en) 2001-02-07 2002-01-29 Phthalimidyl azo dyes, process for the preparation thereof and the use thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP01810127 2001-02-07
EP01810127.9 2001-02-07

Publications (1)

Publication Number Publication Date
WO2002068539A1 true WO2002068539A1 (en) 2002-09-06

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Country Status (14)

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US (1) US7087731B2 (enrdf_load_stackoverflow)
EP (1) EP1358274B1 (enrdf_load_stackoverflow)
JP (1) JP4205951B2 (enrdf_load_stackoverflow)
KR (1) KR100840884B1 (enrdf_load_stackoverflow)
CN (1) CN1249171C (enrdf_load_stackoverflow)
AT (1) ATE496973T1 (enrdf_load_stackoverflow)
CZ (1) CZ20032383A3 (enrdf_load_stackoverflow)
DE (1) DE60239044D1 (enrdf_load_stackoverflow)
ES (1) ES2358986T3 (enrdf_load_stackoverflow)
PL (1) PL362752A1 (enrdf_load_stackoverflow)
PT (1) PT1358274E (enrdf_load_stackoverflow)
RU (1) RU2288242C2 (enrdf_load_stackoverflow)
TW (1) TW593555B (enrdf_load_stackoverflow)
WO (1) WO2002068539A1 (enrdf_load_stackoverflow)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004044058A1 (en) 2002-11-11 2004-05-27 Ciba Specialty Chemicals Holding Inc. Phthalimidyl-azo dyes, process for their preparation and their use
WO2007144298A3 (de) * 2006-06-14 2008-02-21 Dystar Textilfarben Gmbh & Co Dispersionsfarbstoffe, ihre herstellung und ihre verwendung
WO2014016072A1 (en) 2012-07-27 2014-01-30 Huntsman Advanced Materials (Switzerland) Gmbh Disperse azo dyes, a process for the preparation thereof and the use thereof
EP2754696A1 (en) 2013-01-15 2014-07-16 DyStar Colours Distribution GmbH AOX-free navy and black disperse dye mixtures
CN103965094A (zh) * 2013-01-31 2014-08-06 江苏道博化工有限公司 N-甲基-4-氨基-5-溴-邻苯二甲酰亚胺的合成方法
US9493657B2 (en) 2013-01-14 2016-11-15 Dystar Colours Distribution Gmbh AOX-free navy and black disperse dyes
EP3461861A1 (en) 2017-10-02 2019-04-03 DyStar Colours Distribution GmbH High wet fast disperse dye mixtures
US10934435B2 (en) 2016-05-25 2021-03-02 Huntsman International Llc Disperse azo dyes, a process for the preparation thereof and the use thereof

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20050085747A (ko) * 2002-12-19 2005-08-29 시바 스페셜티 케미칼스 홀딩 인크. 프탈이미딜 아조 염료, 이의 제조방법 및 이의 용도
ES2415929T3 (es) * 2008-10-21 2013-07-29 Huntsman Advanced Materials (Switzerland) Gmbh Colorantes azoicos, procedimiento para la preparación de los mismos y uso de los mismos
CN104403348B (zh) * 2014-11-18 2016-09-07 李百春 一种高水洗牢度和升华牢度的紫色分散染料及其制备方法
CN104448892B (zh) * 2014-11-18 2017-04-05 李百春 一种高水洗牢度和升华牢度的宝蓝分散染料及其制备方法
CN104479395A (zh) * 2014-11-18 2015-04-01 杭州福莱蒽特精细化工有限公司 一种高水洗牢度和高日晒牢度的分散染料及其制备方法
CN104448893B (zh) * 2014-11-18 2017-04-05 杭州福莱蒽特精细化工有限公司 一种高水洗牢度和升华牢度的红色分散染料及其制备方法
CN105733291B (zh) * 2016-01-28 2018-03-30 俞杏英 一种高移染红色分散染料单体化合物及其制备方法和应用
CN107129706B (zh) * 2017-05-02 2019-05-17 杭州福莱蒽特精细化工有限公司 一种高染色牢度的分散深蓝染料组合物
CN109054429B (zh) * 2018-07-06 2020-06-09 浙江万丰化工股份有限公司 一种含乙酰胺基团的偶氮染料化合物及其制备方法和应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3980634A (en) * 1973-07-02 1976-09-14 Eastman Kodak Company Phthalimidyl-azo aniline type compounds and polyester fibers dyed therewith
EP0443984A1 (de) * 1990-02-19 1991-08-28 Ciba-Geigy Ag Phthalimidyl-Azofarbstoffe
WO2000040656A1 (de) * 1998-12-31 2000-07-13 Ciba Specialty Chemicals Holding Inc. Phthalimidyl-azofarbstoffe, verfahren zu deren herstellung und deren verwendung

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU910698A1 (ru) * 1980-07-08 1982-03-07 Предприятие П/Я М-5400 Смесовой дисперсный 1,4-диариламиноантрахиноновый краситель дл полиэфирных волокон

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3980634A (en) * 1973-07-02 1976-09-14 Eastman Kodak Company Phthalimidyl-azo aniline type compounds and polyester fibers dyed therewith
EP0443984A1 (de) * 1990-02-19 1991-08-28 Ciba-Geigy Ag Phthalimidyl-Azofarbstoffe
WO2000040656A1 (de) * 1998-12-31 2000-07-13 Ciba Specialty Chemicals Holding Inc. Phthalimidyl-azofarbstoffe, verfahren zu deren herstellung und deren verwendung

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006505662A (ja) * 2002-11-11 2006-02-16 チバ　スペシャルティ　ケミカルズ　ホールディング　インコーポレーテッド フタルイミジル−アゾ染料、その調製方法及びその使用
KR101035841B1 (ko) * 2002-11-11 2011-05-20 시바 홀딩 인크 프탈이미딜-아조 염료 및 이의 제조 방법
WO2004044058A1 (en) 2002-11-11 2004-05-27 Ciba Specialty Chemicals Holding Inc. Phthalimidyl-azo dyes, process for their preparation and their use
WO2007144298A3 (de) * 2006-06-14 2008-02-21 Dystar Textilfarben Gmbh & Co Dispersionsfarbstoffe, ihre herstellung und ihre verwendung
US9376570B2 (en) 2012-07-27 2016-06-28 Huntsman International Llc Disperse azo dyes, a process for the preparation thereof and the use thereof
WO2014016072A1 (en) 2012-07-27 2014-01-30 Huntsman Advanced Materials (Switzerland) Gmbh Disperse azo dyes, a process for the preparation thereof and the use thereof
US10023742B2 (en) 2012-07-27 2018-07-17 Huntsman International Llc Disperse azo dyes, a process for the preparation thereof and the use thereof
US9534118B2 (en) 2013-01-14 2017-01-03 Dystar Colours Distribution Gmbh High wet fast disperse dye mixtures
US9493657B2 (en) 2013-01-14 2016-11-15 Dystar Colours Distribution Gmbh AOX-free navy and black disperse dyes
EP2754696A1 (en) 2013-01-15 2014-07-16 DyStar Colours Distribution GmbH AOX-free navy and black disperse dye mixtures
CN103965094A (zh) * 2013-01-31 2014-08-06 江苏道博化工有限公司 N-甲基-4-氨基-5-溴-邻苯二甲酰亚胺的合成方法
US10934435B2 (en) 2016-05-25 2021-03-02 Huntsman International Llc Disperse azo dyes, a process for the preparation thereof and the use thereof
EP3461861A1 (en) 2017-10-02 2019-04-03 DyStar Colours Distribution GmbH High wet fast disperse dye mixtures
WO2019068443A1 (en) 2017-10-02 2019-04-11 Dystar Colours Distribution Gmbh MIXTURES OF DISPERSED COLORANTS HAVING HIGH WET SOLIDITY
US10800923B2 (en) 2017-10-02 2020-10-13 Dystar Colours Distribution Gmbh High wet fast disperse dye mixtures

Also Published As

Publication number Publication date
DE60239044D1 (de) 2011-03-10
KR20030072402A (ko) 2003-09-13
US20040097716A1 (en) 2004-05-20
RU2003125644A (ru) 2005-03-20
PT1358274E (pt) 2011-04-05
RU2288242C2 (ru) 2006-11-27
ES2358986T3 (es) 2011-05-17
CN1249171C (zh) 2006-04-05
CN1491259A (zh) 2004-04-21
EP1358274A1 (en) 2003-11-05
US7087731B2 (en) 2006-08-08
JP4205951B2 (ja) 2009-01-07
JP2004524408A (ja) 2004-08-12
EP1358274B1 (en) 2011-01-26
TW593555B (en) 2004-06-21
CZ20032383A3 (cs) 2003-11-12
PL362752A1 (en) 2004-11-02
KR100840884B1 (ko) 2008-06-24
ATE496973T1 (de) 2011-02-15

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